Here's a character lineup for the upcoming Dungeonteller RPG release. Left to right, it's elf, paladin, warrior. These are vector files created in Illustrator. I might post a step-by-step tutorial someday but for now, just enjoy. Eventually I hope to have illustrations for both genders for each character class. Next up will be rogue, wizard, and dwarf.
I find that young players REALLY want to know what their characters look like and to see their armor and gear clearly. I've made each piece of gear very "thingy" and concrete-looking. I think that's what people might mean when they describe an illustration as "iconic" -- that each object seems to have its own life and is not subservient to the entire image.
And no one did that better than David Trampier. It's mostly about how he uses negative space and line weight. DAT was intensely aware of the negative space between the lines. If you want a technical reason why Trampier's art is more attractive than Dave Sutherland's, it's that Sutherland has a more limited sense of negative space. His lines are always doing more work to describe form than the white spaces are. In a Tramp drawing, the white space is just as active as the black space. It's anything but empty. (I should say that I think Sutherland was at least Tramp's equal in terms of imaginative power, I'm just talking about his technical ability and aesthetic sensitivity).
Tramp was also more sensitive to line weight. In the salamander illustration, the spear is given "thingy-ness" with a relatively heavy exterior line weight, pushed forward even more by the mass of the body behind it. He understands how varying line weights can accent form and describe textures. Sutherland's line weights are constant and often anemic for the descriptive work they need to perform.
And let's not forget invented patterns, like hatching and crosshatching. If you look at DAT's ilustration for Emirikol the Chaotic, you can identify at least ten invented systems of markmaking, that rigorously describe the textures of stone, a horse's coat, cloth, and so on. If you're going to apply an invented pattern to an object in a drawing, you can't be half-assed or parochial about it. Above all, that's what makes me wince when I look at Sutherland's work. His crosshatching doesn't do much to convey either form or texture, it's just a fill.
I've never been able to find a primary source or written source that describes Tramp's influences, but I'd bet he was strongly influenced by two underground comix artists of the preceding decade: Rick Griffin and Greg Irons. Both of them have the same hyper awareness of black/white and positive/negative balance in their line work. Irons ended up doing the "Dungeons and Dragons Coloring Book" which makes me wonder if Tramp recommended him to the powers that be for that project.
Here are samples of Griffin's and Iron's work. Judge for yourself! If you don't want to stop there, you can reach back to look at the poster art of Mucha and the very granddaddy of them all, Albrecht Durer.